Among a large variety of nitrogen-containing heterocyclic compounds, heterocycles containing an urazole (1,2,4-triazolidine-3,5-dione) moiety are of interest because they constitute an important class of natural and non-natural products, many of which exhibit useful industrial applications. Industrially urazole is used in the manufacture of automobile air bags, as blowing agent in plastics, in the production of herbicides, and antifungal compounds and in polymeric materials.
Urazole can be obtained from 1,2,4-triazoline-3,5-dione (TAD). 1,2,4-triazoline-3,5-dione are known to be enophile and dienophile and readily undergoes cycloaddition reactions such as Diels-Alder (DA) reaction in the presence of suitable DA or ene reactions in the presence of suitable ene reaction partners.
Since its first description in the literature in 1928, the Diels-Alder (DA) reaction has become one of the most known reactions in organic synthesis. The reaction comprises a [4+2] cycloaddition reaction between an electron-rich diene and an electron-poor dienofile (for example an alkene), resulting in the net rupture of two π bonds, and the formation of two σ bonds. The furan-maleimide system (Scheme 1) is the most studied DA system with applications in polymer chemistry. This system however has several drawbacks namely, that the adduct produced from the furan and maleimide DA reaction is prone to hydrolysis. Moreover, the DA-reaction is often slow and requires the use of metal-based catalysts, which present environmental concerns. Another problem that this system presents is that the reactivity of maleimide limits the array of adducts produced. Moreover, as shown in Scheme A, the DA-reaction between furan and maleimide does not proceed at room temperature.

Compounds containing urazole moiety have attracted much interest in recent years. Despite the available synthetic methods, there still exists a need for developing more efficient procedures, which would allow the ready synthesis of new urazole compounds.
It is an object of the present invention to provide new molecules comprising specific urazole moiety and new process for preparing them.